368 total properties
View 1715 KENILWORTH STREET Holiday, FL MLS# S5145157
  • Virtual Tour
1 of 21
$309,999
3

Beds

2.0

Baths

1,442

Sq.Ft.

1715 KENILWORTH STREET

Holiday, FL

View 6345 LOST TRAIL Holiday, FL MLS# W7881056
  • Virtual Tour
1 of 83
$309,000
5

Beds

2.0

Baths

1,920

Sq.Ft.

6345 LOST TRAIL

Holiday, FL

Courtesy of FUTURE HOME REALTY
View 4803 GUARDIAN AVENUE Holiday, FL MLS# TB8487126
$305,900
3

Beds

3.0

Baths

1,712

Sq.Ft.

4803 GUARDIAN AVENUE

Holiday, FL

Courtesy of BUILDING NEST REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 3530 UMBER ROAD Holiday, FL MLS# TB8456171
  • Virtual Tour
1 of 41
$304,999
3

Beds

2.0

Baths

1,424

Sq.Ft.

3530 UMBER ROAD

Holiday, FL

Courtesy of STAR BAY REALTY CORP.
View 3314 COLUMBUS DRIVE Holiday, FL MLS# O6414432
  • Recently Listed with Virtual Tour
1 of 35
$304,900
3

Beds

2.0

Baths

1,513

Sq.Ft.

3314 COLUMBUS DRIVE

Holiday, FL

Courtesy of SUNSET LAKES REALTY, LLC.
View 2453 PLEASANT HILL LANE Holiday, FL MLS# O6364058
  • Adult Community with Virtual Tour
1 of 25
$300,000
2

Beds

2.0

Baths

1,555

Sq.Ft.

2453 PLEASANT HILL LANE

Holiday, FL

Courtesy of LOKATION
View 2211 PLEASANT HILL LANE Holiday, FL MLS# TB8485823
  • Adult Community with Virtual Tour
1 of 40
$300,000
2

Beds

2.0

Baths

1,500

Sq.Ft.

2211 PLEASANT HILL LANE

Holiday, FL

Courtesy of COLDWELL BANKER REALTY
View 5626 MOOG ROAD Holiday, FL MLS# TB8511964
  • Virtual Tour
1 of 38
$300,000
3

Beds

2.0

Baths

1,278

Sq.Ft.

5626 MOOG ROAD

Holiday, FL

Courtesy of LCA REALTY, LLC
View 3332 WILSON DRIVE Holiday, FL MLS# W7884874
  • Virtual Tour
1 of 28
$299,990
3

Beds

2.0

Baths

1,444

Sq.Ft.

3332 WILSON DRIVE

Holiday, FL

View 5338 SPANISH TRAIL Holiday, FL MLS# TB8462546
  • Virtual Tour
1 of 34
$299,900
2

Beds

2.0

Baths

1,212

Sq.Ft.

5338 SPANISH TRAIL

Holiday, FL

Courtesy of CENTURY 21 COASTAL ALLIANCE
View 3127 DOLE STREET Holiday, FL MLS# TB8482547
  • Virtual Tour
1 of 39
$299,900
2

Beds

2.0

Baths

1,184

Sq.Ft.

3127 DOLE STREET

Holiday, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 4301 WESTWOOD DRIVE Holiday, FL MLS# TB8484815
  • Virtual Tour
1 of 13
$299,900
2

Beds

1.1

Baths

1,259

Sq.Ft.

4301 WESTWOOD DRIVE

Holiday, FL

Courtesy of AVENUE HOMES LLC
View 3625 RICHBORO DRIVE Holiday, FL MLS# TB8463808
  • Virtual Tour
1 of 24
$299,000
3

Beds

2.0

Baths

1,587

Sq.Ft.

3625 RICHBORO DRIVE

Holiday, FL

Courtesy of PEOPLE'S TRUST REALTY
View 4344 OAK BLUFF AVENUE Holiday, FL MLS# TB8516133
  • Recently Listed with Virtual Tour
1 of 49
$299,000
3

Beds

2.0

Baths

1,547

Sq.Ft.

4344 OAK BLUFF AVENUE

Holiday, FL

Courtesy of HOMEXPRESS REALTY, INC.
View 4239 WOODFIELD AVENUE Holiday, FL MLS# TB8517188
  • Recently Listed with Virtual Tour
1 of 34
$299,000
3

Beds

2.0

Baths

1,389

Sq.Ft.

4239 WOODFIELD AVENUE

Holiday, FL

View 3228 ROCK VALLEY DRIVE Holiday, FL MLS# TB8467302
  • Virtual Tour
1 of 28
$297,000
2

Beds

2.0

Baths

1,334

Sq.Ft.

3228 ROCK VALLEY DRIVE

Holiday, FL

Courtesy of ENGEL & VOLKERS BELLEAIR
View 3042 BAHIA AVENUE Holiday, FL MLS# TB8504500
  • Virtual Tour
1 of 37
$295,000
3

Beds

2.0

Baths

1,134

Sq.Ft.

3042 BAHIA AVENUE

Holiday, FL

View 1215 PERSIMMON DRIVE Holiday, FL MLS# TB8514707
  • Recently Listed
1 of 30
$295,000
3

Beds

2.0

Baths

1,365

Sq.Ft.

1215 PERSIMMON DRIVE

Holiday, FL

Courtesy of MARK SPAIN REAL ESTATE
View 1039 CLAIRBORNE STREET Holiday, FL MLS# TB8519062
  • Recently Listed
1 of 67
$295,000
3

Beds

2.0

Baths

1,296

Sq.Ft.

1039 CLAIRBORNE STREET

Holiday, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 1012 PRESCOTT LANE Holiday, FL MLS# TB8486952
  • Virtual Tour
1 of 45
$294,900
3

Beds

2.0

Baths

1,492

Sq.Ft.

1012 PRESCOTT LANE

Holiday, FL

Courtesy of CHARLES RUTENBERG REALTY INC

About Holiday

Listings in Holiday, FL

380

Estimated median home price

$239,950
Holiday FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Holiday, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Holiday, FL.

Homes for Sale by Price in Holiday, FL

Price Count
$0 - 100K 33
$100K - 200K 88
$200K - 300K 162
$300K - 400K 58
$400K - 500K 18
$500K - 600K 6
$600K - 700K 3
$700K - 800K 3
$800K - 900K 2
$900K - 1M 0
$1M - Max 7

Homes for Sale by Type in Holiday, FL

Property Type Count
Single Family 258
Townhouse 18
Condo 22
Commercial 4
Rental 74
Lots and Land 25
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 52
Farms 0

(Data as of 6/22/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 6/22/2026.